


Won't you let me know if you feel free

by nearperfectthing



Category: Crooked Media RPF
Genre: Boarding School AU, alternate timeline to the white house, appearances by jon favreau and assorted minor characters
Language: English
Status: Completed
Published: 2020-02-03
Updated: 2020-02-03
Packaged: 2021-02-26 10:34:31
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,388
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22540177
Author URL: https://archiveofourown.org/users/nearperfectthing/pseuds/nearperfectthing
Summary: (1997)"Jon had not intended for Tommy Vietor at all."In which Jon Lovett and Tommy Vietor are best friends in boarding school, don't talk for ten years, and end up at the White House together anyway.
Relationships: Jon Lovett/Tommy Vietor
Comments: 10
Kudos: 59





	Won't you let me know if you feel free

**Author's Note:**

> Special thanks to Molly for her notes on a tommyjon boarding school au, and everyone else who pitched in with help on the details. I don't have the slightest clue what New England boarding school life is like, or, for that matter, what it's like to work at the White House. As some might say, this is some non-fact checked fanfiction. Title is from First Aid Kit's "Postcard". Thanks for reading and for keeping the fourth wall, and I hope you enjoy!

01\. (2009)  
When Jon saw it, only his fourth day in his new job, he almost dropped everything he was carrying. This included three briefing books, two cans of diet coke, one full and one empty, at least three papers you needed security clearance to read, and a speech with notes from the president of the goddamn United States. It, in this case was a neck. It was a nice enough neck, a pale neck with fine hair that, in most lights, bordered in light brown, but right at the back of the neck, at just the right angle, looked almost strawberry blonde. It was a neck that Jon would recognize anywhere, in any context, in any moment of his life. It was a neck that made his heart surge and shrink at the same time. It was the neck of Tommy Vietor, connected to a head that, thankfully, for the moment at least, was turned away from him.

Jon halted in his steps, turned to the side so he could double back down the hallway, fingers clutched around the corner of the briefing book, shaking just enough to jostle the soda in the diet coke bottle. It would probably explode when he opened it. Out of the corner of his eye, Jon could see the neck, and the head attached to it, start to turn. His ears picked up the sound immediately, like they had been waiting to hear it for years. As a matter of fact, it had been almost a decade since his ears had heard this particular sound. It was the sound of a nice voice, Boston brassy but sanded off at the edges by polite New England, and containing an overtone of confusion and a very quiet hint of sweetness. The voice said, “Jon?”

No, Jon thought, you are not messing this up for me, Tommy Vietor. I will not let you mess me up again. He walked away, as quickly as he could, back to the office he had come from. 

02\. (1997)  
Here is how Jon imagined the first day of the school year at boarding school: boys in well pressed uniforms and ties that were carefully knotted to look like their owners didn’t care at all, calling each other by their last names, flashing their hundred dollar watches and talking about summering in the Alps. 

Here is what the first day of the school year at boarding school looked like: boys in well pressed uniforms and ties that were carefully knotted to look like their owners didn’t care at all, calling each other by their last names, flashing their hundred dollar watches and talking about summering in the Alps, as well as summering in southern France and summering in Kennebunkport. Jon got the feeling that by virtue of being in the United States, this last one was considered the least impressive of the option. Jon was pretty sure if he showed up in Kennebunkport, they wouldn’t let him in. Did they even allow Jews there? Or did they have mid-century country club rules?

Jon had spent the break summering at his summer job, stapling papers at neighbor’s law office. The most exotic place he’d gone was Coney Island. 

Deep breaths, Jon. 

The voice in his head that sounded like his mother said, Don’t worry about a thing Jonathan, just be you. The voice in his head that sounded like his father said, It’s a hell of an opportunity Jon, don’t waste it. Generally speaking, things were not going well in Jon’s life when his father’s advice rang more true than his mother’s. 

Jon was wearing the same uniform, same pressed grey suit jacket and white collared shirt and neat red tie. His shoes, brand new, squeaked when he walked, but he was pretty sure he was the only person who could hear that. Outside of being a few inches shorter than everyone else, nothing about Jon should have stood out to his fellow students. But he was so goddamn uncomfortable, it must have been radiating off of him. Jon couldn’t remember the last time he had worn a suit jacket and a tie. Maybe his cousin’s bar mitzvah? He felt like he should be wearing a yarmulke. Now that would make him stand out. 

Here were some facts about Jon’s new school:  
1\. It was founded in 1865 by two priests who wanted to educate New England’s youth in “the most advanced academic and most foundational moral principles,” but had phased out the religious element some time in the 1940s (luckily, or Jon’s parents never would have let him go).  
2\. It still claimed to educate New England’s youth in the most advanced academic and most foundational moral principles, as well as having a cutting edge engineering lab and a nationally ranked crew, lacrosse, and tennis teams.  
3\. It had become a boarding school two years after its founding, and nearly 90% of students boarded year round. 4. The other 10% came from the nearby town, which had a median income of $90,000 per year.  
5\. The school began to accept students of color in 1960, and never accepted female students.  
6\. Almost all students at the high school had also gone to the connected middle school. There was a private elementary school, technically unaffiliated, down the road which served students up until age eleven.  
7\. Nearly 30% of students were given some form of financial aid, but only three students per year were given full scholarships. These scholarships were based on receiving no less than a perfect score on the admissions test, two exemplary essays, and the recommendation of not only former teacher, but the principal of the student’s former school. Students on academic scholarships were expected to maintain at least a 3.7 GPA, which would put them in the top 10% of the class.  
8\. It was even more rare to get an academic scholarship past freshman year of high school, but Jon had. He was entering tenth grade, the only student in the whole class who hadn’t been there the year before. Jon wondered if he should find the other two kids on full scholarship, or if that would make everything awkward and terrible.  
9\. More than a third of students had fathers who went to the school. Of that third, almost 80% had grandfathers who were alumni as well. 

Things Jon knew about himself:  
1\. He had thought he knew what it felt like to be out of place. Stepping into school that day, he began to wonder if he has the slightest clue what he had just gotten himself into. 

03\. (1997)  
Jon’s first class of the day was English. Specifically, it was an American literature class, a review of the American canon that started with the Scarlet Letter and ended with The Grapes of Wrath. Jon liked English classes, usually, and he was a good writer, but he had been a bit apprehensive about this class. Maybe because it seemed so much more serious, nothing like English 10 he would have been taking at public school. Or maybe he was just scared of learning he wasn’t such a good writer after all. 

Which wasn’t half as scary as what actually happened. Which was, the teacher, who was wearing an honest-to-God sweater vest asked “our new student” to stand up and “introduce himself.”

“Uh,” Jon started. “I’m Jon. Lovett.” He started to sit down. 

“Tell us about you,” the teacher said, “Where are you from? What brings you here, to study among New England’s finest?”

Was he supposed to be funny? Show off? “Um,” Jon said, “I’m from Long Island.” He was suddenly deeply, horribly aware of the way his voice sounded, whether he had any trace of a New York accent. “And, uh, I’m here for,” Be funny, Jon. Maybe they’ll like you if you’re funny. “I’m here as a sociological experiment?”

Dead silence. And then, at the desk right in front of him, Jon hear a tiny giggle. The teacher, whio pretty obviously had no idea what to do with Jon, moved on to the actual lesson plan for the day. In front of Jon, the kid who had giggled turned around. From the back, all Jon had noticed was his very blonde hair and very solid seeming neck. But looking into his face, Jon couldn’t help but notice how attractive the boy was, his straight nose, his blue eyes. 

“That was funny,” the boy said. 

Jon just stared. Were the boy’s eyes actually gray? Gray-blue? Blue-gray?

“I’m Tommy,” the boy said, and then he turned back around, leaving Jon to stare at the neatly combed hair on the back of his head. The teacher moved on to talking about Nathanial Hawthorne. 

Jon’s next class of the day was math, where he did his best to lose himself in trigonometry and forget the rest of the day, except that Tommy’s pretty blonde head kept floating out of the textbook at him. 

04\. (1997)  
The thing about boarding school is that it was not content with interfering with your academic life, it also had to wind your way into every moment of your personal life. Jon hadn’t been in any school clubs before, because he hadn’t wanted to spend an extra moment at school more than he had to. And also because even Jon was socially-aware enough to know that joining math decathlon was a social killer. But in his new school, Jon was required to participate in an extracurricular, and competitive math was still a social disaster. 

Look, Jon knew he was gay. He had never told anyone else, not even his mother, who he was almost positive wouldn’t hate him for it. But Jon held a secret hope that New England boarding school was at least half as homoerotic as the movies had made them out to be, and since he didn’t know how to join the Dead Poet’s Society, drama club seemed his best chance to meet someone gay. And Jon didn’t have the self-esteem to actually audition for the fall play (they didn’t do musicals, which didn’t seem to bode well for Jon’s chances at meeting other gay guys) which is how he ended up running lights. 

He sat up in the balcony, trying to keep up with cues and following the actors around with the spotlights. He felt enormously powerful, in that spot, like he was in control. He was also alone, which didn’t bother him at first. After all, boarding school was an intensely social experience, dining halls and dorms and it was nice to have some time sitting alone away from the rest of the world. But a few months into the year, Jon really hadn’t made any friends, which meant that he was spending a lot of time being quiet, which was not Jon’s natural state. Somehow, he hadn’t been worried about being homesickness when he chose boarding school, but he found that he missed the comfort of being around people he knew, bouncing his jokes off of his mom quite a bit. In any event, by the time the drama club was about to start rehearsing in earnest, Jon was quite lonely. Which is maybe why Jon ended up spending so much time watching people construct the set. 

The drama teacher had entrusted the set-building to the lacrosse team, which didn’t have competitions in the fall. The coach, who was famously a hardass, would scratch people from games for missing a practice and kick them off the team for missing a game, didn’t want his team to go the whole fall without serious workouts, and so he had lent them out to build the set. which is how Jon came to be watching Tommy from his English class hauling set pieces across the stage for three hours a week. And from his perch in the balcony, controlling the lights, no one could see as Jon trained his eyes on Tommy’s thighs, Tommy’s shoulders, Tommy’s… Jesus. Jon needed a life.

05\. (1997)  
At Syosset High, they had flushed his gym clothes down the toilet. Jon had locked himself in a bathroom stall in the changing room, blinking tears out of his eyes, thinking that maybe at least this would get him excused from gym class for a few days.

Jon hadn’t said anything to his teachers, because he wasn’t stupid, and he’d made that mistake once before. But it didn’t take much to figure out who was responsible, they laughed under their breath every time he walked into gym class. That was the day he started wondering if he could go somewhere else for school.

In the time it took for Jon to find his new school, figure out the application and scholarship process, he three more mishaps had become his gym uniform, two entire hot lunches were spilled over his lunch table and one over his math textbook, he responded better to homophobic slurs than his own name, and they’d thrown him in a goddamn recycling bin. Jon didn’t just want out, he needed out. 

His mom didn’t know but she knew something, enough to help him convince his dad it was a good idea. Boarding school sounded insane but after all, it was a scholarship, and Jon was smart, and maybe this would be good for him. Get a good education, make some connections. See the world outside of Long Island. And so the week after his fifteenth birthday, Jon and his mom packed up a suitcase of his favorites books and clothes and video games and they drove up to Massachusetts. 

Here was the goal: new school, nobody had to know the old Jon Lovett. Jon intended to ace his classes, stay in the closet, and maybe, make some friends. 

Jon had not intended to see Tommy Vietor smile at him like that, an almost goofy smile that broke Tommy’s serious, porcelain-WASP face in half. Jon had not intended for Tommy Vietor at all. 

06\. (1997)  
What made it so hard was, Tommy was friendly too. It started in their English class, just an occasional smile Tommy would shoot over his shoulder. It continued when they had to pair up for an assignment, which they got an A on. And then one day Tommy said, as Jon was packing up his books, “So what’s the deal with the modern scenery?” To be honest, Jon had no idea what he was talking about. 

“The modern set, for the play. It’s Shakespeare, right? So why all the fake graffiti on the set pieces?”

Jon was pretty sure that the director was trying to inject some sort of edginess into a boarding school production of the Merchant of Venice, or maybe just it was easier to make costumes for a modern setting. He was also thinking about how he had never directly acknowledged that he and Tommy spent their afternoons together in the theater, Tommy building sets and Jon managing the lights, sitting around and staring at Tommy. Which had potential to be incredibly embarrassing. 

Tommy interrupted those thoughts. “That thing you said on the first day,” he said, “it was really funny. I haven’t heard you say anything funny since.”

“Ouch,” Jon said.

“I didn’t mean it like that. I meant, you hardly say anything not directly related to school. But I know you’re funny. You can be funny.”

So then along with the smiles and the greetings and the group projects, Jon began to whisper the occasional joke in Tommy’s ear, a dumb pun or a quiet insult or a dear diary, and Tommy would giggle that same giggle Jon had heard on the first day. 

07\. (1997)  
Six ways Jon Lovett’s social standing changed when he went to boarding school:  
1\. At first it was better. New England’s finest didn’t stoop to homophobic slurs, to pushing and shoving.  
2\. But New England’s finest had no problem with the more subtle ways to make Jon know exactly how different they saw him. The familiar “cocksucker” or “pussy” was quickly replaced with a jovial “people like you, Lovett”. “People like him” were a variety of things. When they weren’t gay, they were scholarship kids, or Jewish, or just not from Massachusetts.  
3\. Jon found that he wasn’t the only person who wanted to talk politics. He had to be careful though, where he quickly learned that arguing was considered quite rude. At home, the realest conversations Jon had with his father were when they yelled at each other about current events. But at school, the tone was harder to judge. Sometimes, it felt like a friendly teasing when the other guys called him a socialist. Most of the time, it felt like an insult.  
4\. The last Friday of each month they didn’t have to wear uniforms. Which is how Jon learned that there was also an unofficial uniform, polos and chinos and Sperrys with striped socks, always striped socks. Jon had never owned striped socks in his life, or boat shoes, or anything that wasn’t a pair of jeans and a t-shirt with some sort of bad science joke on it. The first few times the no-uniform day came around, Jon felt horribly awkward, spend most of the day hiding in the dorms. And then the science shirts became a sort of armor, a reminder that he was a person outside of this school.  
5\. Some people went home on the weekends. Some people went on elaborate trips, came back with new clothes they could only wear once a month, telling stories about the bars they had hit up and the girls they had made out with. Jon mostly stayed at school, trying not to waste the allowance his parents sent him to school with. On the occasion that someone asked him how he had spent the weekend, Jon sometimes felt the urge to lie, come up with something more exciting than whatever mediocre sitcom he had watched in the empty common room, which premade cookies he ate until he regretted everything in his life.  
6\. But Tommy was there. And Tommy was not like everyone else. 

08\. (1998)  
Tommy was a nice guy, he presented with a certain mellowness, deferential to teachers, friendly to the other guys, with occasional bursts of humor that could get a whole class laughing. Jon figured it was something about the way Tommy acted, the way he looked, maybe it was the lacrosse team. 

But Tommy could be mean too, a thick coat of sarcasm that could come across as earnest if you didn’t know him too well. Jon saw it first in the way he talked to the guys who sat right in front of Tommy in their English class, when the guys would mock the teacher or someone else in the class with a fake-serious answer. “That’s a great point!” Tommy would say, loud enough for the guys to hear, and then just quiet enough for Jon, “It’s so nice that your dad is still doing your homework from inside his insider-trading jail cell. That kind of connection can mean a lot to a kid.” 

“Sir!” Tommy would exclaim, when their history teacher explained with great conviction that all Americans were better off when people worked for themselves, didn’t waste the time of the government or the taxpayers on welfare. “It is such an honor to meet Mister Ronald Reagan himself, sir!” And there was Jon, laughing in the background, receiving the dirty glares of the other guys who wouldn’t dare pick a fight with Tommy, who was popular and athletic and cool. 

There was actually one other situation in which Tommy’s biting sarcasm came out: when they were insulting Jon. This came in a more subtle form, never calling too much attention, just enough that Jon was distracted from the original insult, entertained by the response. Jon couldn’t help but feel a little touched, a little smug. Maybe a little hot under the collar. 

09\. (1998)  
Tommy knew how to drive a speedboat. It was not strictly legal for Tommy to drive a speedboat, but he totally could. Jon learned this one weekend shortly into their junior year, when Tommy invited him home for a long weekend. Not home to the suburbs of Boston, but home to the summer house on the Cape. New England WASP life was ridiculous. Not to mention the fact that the summer house on the Cape, which was right on the water, also included a dock and an honest-to-God speedboat. 

Which is how they ended up on a Saturday afternoon, speeding down the shore, sun beating down on their necks. It was a weekend Tommy didn’t have lacrosse practice, the thing that usually kept him on campus with Jon. Tommy kicked his shoes off, (“Don’t tell my mom I was driving the boat barefoot” “I thought I wasn’t supposed to tell your mom you were driving the boat at all.” “Yeah well,” Tommy said, laughing freely like he didn’t have a care in the world, “don’t do either.”) Tommy also pulled off his shirt, rubbing sunscreen on his shoulders while Jon tried to avert his eyes. Tommy burned later, pointing it out and laughing at himself. Jon laughed along with him, grateful for the excuse to look at Tommy’s bare chest. 

The wind off the ocean and the speed of the boat blew the hat off Jon’s head. “You’re polluting the water,” Tommy said, horrified, “what kind of Democrat are you? Al Gore would be ashamed.”

“My dad will kill me if I lose that Mets hat,” Jon said, “He’s already convinced I’m forgetting ‘my roots’, like I’ve ever cared about sports.”

“The Mets suck anyway,” Tommy said. They chased the hat down in the boat, until Tommy cut the engine and, without warning Jon, dove over the side of the boat and swam to grab the hat. He hauled himself back onto the boat, dripping and grinning all over Jon’s hair, curls messed up from the wind, as he ever so gently placed the hat back on Jon’s head. 

“Hey Jon,” He said, “Do you think your Dad will like me now?” It took everything in Jon not to ask why Tommy wanted to know. 

10\. (1998)  
Tommy had told Jon that when he was younger, he was obsessed with little pranks, scaring his sister with fake bugs, he even confessed to having owned a whoopie cushion. He had made crank calls whenever he had been home alone, or sometimes not, holed up in his room laughing too quietly for his mom to notice and worry what he was doing up there alone.

“When you say ‘when you were younger’,” Jon said.

Tommy laughed. “Yeah, I stopped, like, sophomore year.”

They had met sophomore year. Sometimes Jon wondered if this timeline meant anything. In good moments, he thought that Tommy had been bored before they met, that Jon had filled some void better than any crank call ever could. In bad moments, he thought he had drained all of the fun from Tommy, who now had to spend his time with an awkward, mildly neurotic nerd who could never fit in. Usually, he figured Tommy had just aged out of it. 

Once, Jon had asked Tommy what he had seen in him in that freshman year English class. “You just seemed interesting,” Tommy had said, “Like someone I wanted to know.” Jon desperately wanted to ask more about this, but it seemed like even more exposing than asking the question to begin with. “And you were funny,” Tommy added.

Jon knew he was funny. Jon knew that Tommy thought he was funny. It was a wonderful thing, Jon would never want to downplay the feeling of making a joke and knowing halfway through he was going to get a laugh. And Jon thought Tommy was funny too. But lots of things were funny, sitcoms were funny, the crank calls Tommy had made as a bratty pre-teen had probably been funny. Surely, there was something more than thinking a person was funny. Late at night, in the dark, Jon desperately wanted Tommy to tell him straight out what Tommy saw in him. And maybe then, maybe then Jon would be able to return the favor. 

11\. (1999)  
Tommy liked to sit on his windowsill, legs dangling outside and down the side of the building. To Jon, they looked impossibly long. The position always felt vaguely unstable when Jon tried it himself, like he could hear his mother’s voice in his head saying, that’s what I send you to that pish-posh school for? So you can risk your neck sitting out a window? But God Tommy made it look elegant. 

He was sitting there, with his feet out the window, on Friday afternoon when Jon showed up at his dorm room. He had brought a bag of gummy bears, which were kind of gross but also really great, and he was totally fixated on Tommy’s socked feet, his heels bumping against the bricks right below the third floor window. 

“Those for me?” Tommy gestured broadly towards the gummy bears, enough to jolt Jon out of his focus on Tommy’s white and yellow patterned socks, which was probably for the best. 

Jon handed the gummy bears over, and leaned against the windowsill, keeping his body inside the window. Jon could feel Tommy’s strong shoulder pressing into his own, Tommy’s weirdly pointed elbow digging into Jon’s side, the curve of Tommy’s thighs in his jeans, pressing against Jon. He could hear Tommy’s even breathing, the sound of chewing on gummys which should be gross but somehow Jon didn’t mind. Jon was deeply grateful that he was facing inside the room, Tommy facing out, so that he didn’t have to look Tommy in the eye. They sat, passing gummy bears back and forth.

“It’s a nice night,” Tommy said. New England WASPs, Jon had learned, really did default to talking about the weather. 

“When we go to the Cape, in the summer, you can really see the stars. Especially when we take the boat out at night. It makes my mom nervous, but it’s the most beautiful thing I’ve ever seen.”

Usually, Jon would take the chance to make fun of Tommy, his rich boy New England upbringing, maybe ask him if his family’s boat was the Mayflower. He didn’t say anything. 

“I’m really glad you’re here,” Tommy said. “Here at school, but also here here. With me.” Jon was hyper aware of the placement of every part of Tommy’s body, pressed against him, which meant he was hyper aware when Tommy’s hand moved, pressed fingers gently into Jon’s side, just above his waist.

Jon turned his head, and Tommy was already there. Looking at his face like he saw something beautiful. Leaning into Jon’s space. Kissing him. Pulling back, just for a moment, letting Jon lean forward and kiss him back. Dear diary, Jon thought, helplessly. 

Tommy moved his other hand, reaching around to cup Jon’s cheek. The bag of gummy bears dropped out of the window, falling the three floors down. Neither of them looked away to find out where it landed. 

12\. (1999)  
Tommy went home, for the weekend. He texted Jon, a few times, mostly normal check-ins. Jon spent the weekend hauled up in his dorm, trying to study for a history exam, and binge-eating Chips Ahoy. On Sunday night, Tommy came back, knocking on Jon’s dorm room door.

“Did you bring me something good?” Jon asked, standing in the doorway. “Taco Bell? Dominos? I’ll take a sleeve of oreos in a pinch.” Tommy grinned at him, sweetly, almost idiotically. Jon found himself, helplessly, smiling back. Tommy pushed his way into Jon’s room, pressing his shoulder firmly against Jon to move him out of the doorway. Jon felt hot all over. For the briefest moment, he wondered if the kiss had been a dream, some strange fantasy.

Tommy sat on Jon’s bed, lounging back against the pillows, smiling with all the certainty in the world. 

“You’re pretty forward,” Jon said. He sounded ridiculously, embarrassingly breathless. Tommy raised an eyebrow, and Jon tried desperately to gather his thoughts. “Dear diary,” he started, weakly, “you’ll never guess–” Tommy was laughing before he could finish the sentence, laughing at the incredibly stupid joke and Jon was on the bed and Tommy was kissing him again and Tommy was kissing him again and Tommy was kissing him again.

They went to class on Monday, and then went back to the dorms together. Jon had never been so aware of his lips in his entire life, and had never been less uncomfortable with the awareness of his own body. 

On Tuesday, more of the same. On Wednesday, they skipped everything, class and extracurriculars and even dinner, lying in the dorms watching daytime tv and kissing some more. And, if Jon was being honest, there was a little bit more than kissing. Who would have ever thought grinding against Tommy’s thigh in a school-issue uniform could be such a transcendent experience? (Actually, Jon could have guessed. He may or may not have thought about it before.) 

On Thursdays, Jon tutored a freshman in geometry, and then Tommy had lacrosse games, and then they would meet for post-game junk food and to study for the weekly quizzes they had in history.

Jon went to tutor the freshman. He came back, ate dinner, waited in his room for Tommy to knock on his door. When their normal meeting time came and passed, Jon went to Tommy’s room, already eager to get a move on. Stupid, it had only been a few hours, but after the way his last few days had gone, it felt like an eternity. No one was in Tommy’s room.

He should have known, Jon realized in retrospect, that something was wrong. But it wasn’t until their class the next day. Tommy was already sitting down to take the quiz, Jon running just on the edge of late, like usual, and Tommy didn’t look up to say hi, that Jon knew. Jon stared at the side of Tommy’s head, willing him to turn. He failed the quiz. And Tommy didn’t look at him.

13\. (1999)  
If Tommy was going to be mad about something, fine. If he had decided this was one giant mistake, that he wanted to forget about it, that he wasn’t gay after all or even worse (would it be even worse?) he was gay but he didn’t want Jon, fine. Let him sulk, let him bury it, and let him come back to Jon and they could start over, pretend everything was okay. That was fine, Jon could do that. He could pretend. 

Tommy didn’t say anything to him.

It was two weeks after they had sat in Tommy’s window, that Jon thought to go check in the bushes below Tommy’s dorm. The bag of gummy bears was long gone. Jon sat there, behind the bushes, back to the brick wall of the dorm, praying no one, praying Tommy, wouldn’t look out the window. And he cried. 

14\. (2000)  
Jon graduated with a 3.9 and a full scholarship to Williams College, where he studied math. He made friends, even good friends. He kissed boys. He went to improv meetings with increasingly un-funny groups of people. 

15\. (2004)  
From Monday to Friday, Jon filed papers as a paralegal. On Friday nights he went to comedy clubs. Sometimes to perform, sometimes to watch. Sometimes his audience laughed until they cried, sometimes he could hear every time the corner of a napkin crumpled. Once, he had half a glass of a rum and coke thrown all down his t-shirt. On Saturday mornings, he stared down at an LSAT prep book until his vision blurred. On Saturday afternoons, he lay on his couch and watched Fraiser. 

16\. (2005)  
Funny enough for a senate staffer, not for the comedy club circuit: the Jon Lovett story.

17\. (2006)  
Jon considered law school again. 

18\. (2006)  
Funny enough for Hillary Clinton, not for the comedy club circuit: the Jon Lovett story, which his mother told with a distinct note of pride in his voice. Jon wondered if anyone in the world loved Hillary Clinton as much as suburban Jewish mothers in New York. 

19\. (2008)  
Jon had just started fantasizing about his office in the White House when the lost in Iowa. They lost. 

20\. (2008)  
Jon really, really didn’t want to go to law school. And he couldn’t handle another trip around the comedy club circuit. 

21\. (2008)  
Jon was lying on his couch when he got the phone call from Isaac. 

“What are you doing?”

Jon told the truth. “Watching Fraiser.”

“I mean with your life.”

“Watching Fraiser.”

Isaac didn’t stoop to respond to this. “The transition team is hiring.”

Jon was pretty sure he knew what this meant. He was pretty sure he didn’t want to think about it too hard. “Hm?”

“The White House transition team. They’re hiring speech writers. I think you should apply.”

Jon forced a laugh. “Like they’d hire me. Remind me again what the last entry on my resume is?”

“They’re hiring us,” Isaac said. “I got hired. It’s a show of unity. Besides, it’s an anonymous contest. And doesn’t Favreau like you, anyway?”

Jon didn’t have anything to say to that.

“Just try it Jon, please? It’s the White House. The fucking White House. Don’t make me come back to New York and kick your ass off that couch, I know you want it as much as anyone.”

It was the fucking White House. So Jon tried it. 

22\. (2009)  
Jon was given a badge with his name on it, which got him through security at the OEOB. He tried not to stare too much at the badge, because it would be pretty embarrassing if someone caught him at it. Look like you fit in, Jon. Now there was something he had practiced at boarding school. 

Jon Favreau met him at the communications office. He was a friendly guy, laughed at Jon’s awkward jokes and makes a few of his own (they were bad, oh God his jokes were so bad, no wonder they hired Jon). Favreau told Jon about the other guys on the team, the other young idealistic work-hard-party-hard Obama staffer stereotypes that Jon had agreed to spend his time with. 

(It didn’t occur to him until later that he had seen that opportunity, the White House (the fucking White House!) as very similar to boarding school – an opportunity that you take, not because you think it will be fun, not because you think you will fit in, but because you’d have to be fucking stupid to pass it up. It took him even longer to realize that there was something about Favreau that had immediately recalled Tommy to him, the bro-y-ness that made Favreau popular, easy to imagine at a party, but a seriousness that made him kind. Somewhere, in the back of his mind, Jon had realized that Favreau was going to do for him was Tommy had done so many years before – make this experience not just bearable, but good.)

Clearly some memo had been passed around (the Obama staffers were big on memos, Jon quickly learned) not to harass the new guys too much. Isaac had been right, it was a show of unity, and Isaac had been right, Favreau did, inexplicably, like Jon. The other staffers invited Jon out to drinks, to dinners that ended up being take-out in their offices at 11 pm, and Jon began to feel, more or less, comfortable. 

(Stupid, he thought later, to think that it could last.) 

23\. (2009)  
It wasn’t that Jon hadn’t known. It wasn’t that, from time to time, he hadn’t searched for Tommy’s name. From time to time, he actually skimmed the newsletter his high school sent out, seeing what his former classmates were up to in their various wealthy and connected roles. And of course, Jon was in politics and he knew the other names in politics, the other young and successful (more successful) people. Which is to say, he knew Tommy was on the Obama campaign. He knew Tommy was in the White House, somewhere. He just wasn’t expecting to run into Tommy during his first week on the job. 

“Jon?” Tommy’s voice said. It was such a familiar voice. It was a voice that sounded like late nights in the common room, like laughter over the motor of the speed boat and the wind, like heels knocking out the side of a window ledge, like a small giggle in front of him on the first day of sophomore year English class. 

It made Jon’s heart constrict. It made him want to throw up, just a little. It made him want to throw his arms around Tommy’s shoulders, to hug him and laugh and cry and say how much he had missed Tommy. 

The empty Diet Coke can went rolling out of Jon’s arms. He scrambled after it, acutely aware of how awkward he felt, blocking people’s way in the hall, people who were supposed to be doing important things, because they worked in the White House god damn it. Acutely aware that Tommy was staring after him as he grabbed the soda can, scrambled to his feet, and headed off the way he came.

Well. Jon had known he would run in to Tommy eventually. Of course it had gone as badly as possible. 

24\. (2009)  
For three whole weeks, Jon managed to push it to the back of his head. And then one day, as he was leaving the office far too late one night after finishing yet another last-minute speech on the stimulus, Tommy was standing outside waiting out Jon’s scooter.

“Jon said you were the one with the fucking electric scooter.” It took Jon a moment to realize that the “Jon” Tommy was referring to was Favreau. He felt suddenly horrifically sad that he was no longer the Jon in Tommy’s life. Which wasn’t fair. It had been more than a decade. Fuck. It had been more than a decade. 

“Hey,” Tommy said.

‘Look,” Jon said, already turning away, “I need to go home.”

“Jon–”

“It’s late, I need to get home.”

“Jon.”

“Tommy. What do you want from me?”

“Can we talk?” Out of Tommy’s mouth, it sounded more like a demand than a request. 

“Right now?”

“It can be later. But please Jon, I need to talk to you.”

“Why?”

Tommy paused, a long moment. It had been more than a decade, and Jon could no longer read the expressions on his face. And then he gave the most tentative, terrified little smile and said, “call it a sociological experiment?”

And Jon couldn’t help it. He softened, just a little. And Tommy must have noticed, must have known somehow. 

“Jon, it’s so good to see you again.” 

“Okay,” Jon said. “Okay.”

25\. (2009)  
He had made a lot of mistakes, Tommy had explained. And it was just – do you remember Rutherford? Coach Rutherford, for the lacrosse team?

Jon couldn’t believe he was getting dragged back into high school drama. Yes, he remembered the lacrosse coach, who was so strict, the one who made Tommy (and the rest of the team, but most relevantly Tommy) build sets for the school play, the one who never let them miss practice. Sure, Jon still remembered, but he was 27 years old, and he wasn’t sure he still cared.

“What about him?”

Tommy paused for a long minute, like he hadn’t had days, years, to think about what he was going to say. “I missed practice with you. Do you remember, we skipped class? It was a Wednesday. I had lacrosse practice on Wednesday.”

Jon hated the fact that he knew just which Wednesday Tommy was talking about. He hated the fact that he knew Tommy was telling the truth about the schedule, that these were details he could have independently confirmed to anyone who had asked about it, if Jon had ever talked about it. He hated himself, in that moment. 

“I skipped practice to be with you and I got in trouble. That’s all, I got scratched from the game the next day. And I just– freaked, I guess. I just freaked.”

Jon crossed his arms. He wasn’t sure whether it was more a gesture of anger or of protection. “You didn’t talk to me, your best friend, the guy you’d just decided you wanted to kiss, for almost ten years, because you didn’t get to play one stupid lacrosse game?” 

Forget it, Jon didn’t hate himself anymore. He hated Tommy. He’d never hated Tommy so much, not even in those awful first days when he realized that Tommy wasn’t going to talk to him again, days he spent curled up in a ball on his bed, eating food from the vending machines until he worried he’d lose his scholarship if he didn’t get up again. Not even those awful days that followed those first awful days, when he squared his shoulders and headed back into the tiny, spiteful world of boarding school to hear the murmured insults launched at him and not have Tommy at his back. 

Tommy opened his mouth to speak, but Jon beat him to it. “Fuck that excuse, Tommy. Fuck you.”

“Well fuck you too.” Tommy’s tone was almost bratty, but Jon could hear the current of real frustration under it. “You said you would hear me out.”

“I never said that.”

“Well you implied it. Please, just listen?” Jon wasn’t sure he could move if he wanted to, so he listened. 

“I know it sounds stupid and childish but we were, Jon. We were stupid and childish. And I was scared that I was going to fuck up my whole life because the things I felt about you were so strong, I’d never felt anything like that before. Jon, I hadn’t even known I was gay. I was scared, and I needed a minute to figure it out and yeah, I shut you out, but you shut me out too, Jon. I didn’t go anywhere. But you were too busy hiding in your room and being too smart for the whole fucking world, it was too late.”

This was not how Jon remembered being at all. Not too smart for the whole fucking world. Too sad, maybe. “You never made a single fucking indication that you were open to that, you can’t put this on me.”

“I don’t know how you made me out to be this, mature, together person Jon,” Tommy said. “I didn’t have my shit together at all, and I was scared, and I was confused, and I was overwhelmed. I don’t know why you treated me like an adult when you never treated yourself like one.”

Well. Fuck. 

“I’m sorry. That was mean,” Tommy paused. “That’s all, now you know. You can go back to ignoring me or whatever the fuck. I’ll tell Favs not to invite me to anything you’re going to be at.”

Which was an option. Maybe Jon could go the next four years, eight years, how ever long he was going to have this job, ignoring Tommy, pretending like it didn’t matter and he had never cared. Jon was pretty sure he couldn’t go the next four minutes, though. Here was Tommy, a little bit mean, a little bit funny, a good to the core, trying to explain a stupid mistake he’d made a decade before. 

“Just now, earlier,” Jon said. “You said you were happy to see me.”

“Okay?” Tommy said. He looked poised to leave.

“Okay.” Jon said. “So I’m happy to see you too.”

Tommy paused. He took this in, he nodded and then he cracked the sweetest, shyest smile Jon had ever seen. It wasn’t Tommy’s normal smile, the one that happened all around his eyes. It was just a little quirk, a question. 

“Dear diary,” Tommy said, “You’ll never believe who I ran into today.”

And Jon laughed. 

26\. (2011)  
“My kids,” Jon announced one sunny Saturday, sitting on the couch with one leg tucked under him and the other flung into Tommy’s lap, “will not go to boarding school.”

“Your kids?” Tommy said.


End file.
